Debenzylation of tertiary amines using phosgene or triphosgene: An efficient and rapid procedure for the preparation of carbamoyl chlorides and unsymmetrical ureas. Application in carbon-11 chemistry

Journal of Organic Chemistry

Volumn 68, Issue 19, 2003, Pages 7289-7297

  Lemoucheux, Laurent ^a   Rouden, Jacques ^a   Ibazizene, Méziane ^a   Sobrio, Franck ^a   Lasne, Marie Claire ^a  

^a UNIVERSITÉ DE CAEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROCHLORIC ACID; POSITRON EMISSION TOMOGRAPHY; STOICHIOMETRY; UREA;

DEBENZYLATION;

AMINES;

CARBAMOYL CHLORIDE DERIVATIVE; CARBON 11; CHLORIDE; COPPER DERIVATIVE; CYANOCUPRATE; NICKEL; PHOSGENE; PIPERAZINE DERIVATIVE; PIPERIDINE DERIVATIVE; PYRIDINE; QUINOLINE DERIVATIVE; TRIETHYLAMINE; TRIPHOSGENE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; DEALKYLATION; METHODOLOGY; POSITRON EMISSION TOMOGRAPHY; REACTION ANALYSIS; STOICHIOMETRY; SYNTHESIS;

EID: 0141677927     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0346297     Document Type: Article

References (70)

1. Fowler J. S., Wolf A. P. Acc. Chem. Res. 1997, 30, 181-188.
2. McCarthy, K. E. Curr. Pharm. Design 2000, 6, 1057-1083.
3. For general references on practical PET chemistry, see: (a) Fowler, J. S., Wolf, A. P. In Positron Emission Tomography and Autoradiography: Principles and Applications for the Brain and Heart; Phelps, M., Mazziota, J., Schelbert, H., Eds.; Raven Press: New York, 1986; Chapter 9.
4. (b) Radiopharmaceuticals for Positron Emission Tomography: Methodological Aspects; Stöcklin, G., Pike, V. W., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1993.
5. (c) Langström, B.; Kihlberg, T.; Bergström, M.; Antoni, G.; Björkman, M.; Forngren, B. H.; Forngren, T.; Hartvig, P.; Markides, K.; Yngve, U.; Ögren, M. Acta Chem. Scand. 1999, 53, 651-669.
6. Hegarty, A. F. In Comprehensive Organic Chemistry; Sutherland, I. O., Ed.; Pergamon Press: Oxford, 1979; Vol. 2, Chapter 9.10.
7. Mills, R. J.; Taylor, N. J.; Snieckus, V. J. Org. Chem. 1989, 54, 4372-4385.
8. Lemoucheux, L.; Rouden, J.; Lasne, M.-C. Tetrahedron Lett. 2000, 41, 9997-1001.
9. (a) Holmes, D. L.; Smith, E. M.; Nowick, J. S. J. Am. Chem. Soc. 1997, 119, 7665-7669.
10. (b). Wang, G. T.; Chen, Y.; Wang, S.; Sciotti, R.; Sowin, T. Tetrahedron Lett. 1997, 38, 1895-1898.
11. (c) Nowick, J. S.; Holmes, D. L.; Noronha, G.; Smith, E. M.; Nguyen, T. M.; Huang, S.-L. J. Org. Chem. 1996, 61, 3929-3934.
12. Saegusa, T.; Tsuda, T.; Isegawa, Y. J. Org. Chem. 1971, 36, 858-860.
13. Kihlberg, T.; Karimi, F.; Langström, B. J. Org. Chem. 2002, 67, 3687-3692.
14. Karimi, F.; Langström, B. Org. Biomol. Chem. 2003, 1, 541-546 and references therein.
15. (a) Schindler, N.; Plöger, W. Chem Ber. 1971, 104, 969-971.
16. (b) Hasserodt, U. Chem Ber 1968, 101, 113-120.
17. (a) Volford, J.; Knausz, D.; Meszticzky, A.; Horvath, L.; Csakvari, B. J. Labelled Compd. Radiopharm. 1981, 18, 555.
18. (b) Hoshino, O.; Saito, K.; Ishizaki, M.; Umezawa, B. Synth. Commun. 1987, 17, 1887-1892.
19. (c) Birkofer, L.; Krebs, K. Tetrahedron Lett. 1968, 885-888.
20. (d) Dean, D. C.; Wallace, M. A.; Marks, T. N.; Melillo, D. G. Tetrahedron Lett. 1997, 38, 919-922.
21. Schirbel, A.; Holschbach, M. H.; Coenen, H. H. J. Labelled Compd. Radiopharm. 1999, 42, 537-551.
22. (a) Landais, P.; Crouzel, C. Appl. Radiat. Isot. 1987, 38, 297-300.
23. (b) Link, J. M.; Krohn, K. A J. Labelled Compd. Radiopharm. 1997, 40, 306-308.
24. (a) Lidström, P.; Bonasera, T. A.; Marquez-M, M.; Nilsson, S.; Bergström, M.; Langström, B. Steroids 1998, 63, 228-234.
25. (b) Lidström, P.; Bonasera, T. A.; Nilsson, S.; Langström, B. J. Labelled Compd. Radiopharm. 1997, 40, 788-789.
26. (a) Crouzel, C.; Mestelan, G.; Kraus, E.; Lecomte, J. M.; Comar, D. Appl. Radiat. Isot. 1980, 31, 545-548.
27. (b) Roeda, D.; Tavitian, B.; Coulon, C.; David, F.; Dollé, F.; Fuseau, C.; Jobert, A.; Crouzel, C. Bioorg. Med. Chem. 1997, 5, 397-403.
28. (c) Hammadi, A.; Crouzel, C. J. Labelled Compd. Radiopharm. 1991, 29, 681-689.
29. (a) Dollé, F.; Valette, H.; Hinnen, F.; Vaufrey, F.; Demphel, S.; Coulon, C.; Ottaviani, M.; Bottlaender, M.; Crouzel, C. J. Labelled Compd. Radiopharm. 2001, 44, 785-795.
30. (b) Crouzel, C.; Hinnen, F.; Maitre, E. Appl. Radiat. Isot. 1995, 46, 167-170.
31. (c) Conway, T.; Diksic, M, J. Nucl. Med. 1988, 29, 1957-1960.
32. Rousseau, A. H.; Diksic, M.; Van Lier, J. E. Int. J. Appl. Instrum. B 1992, 19, 175.
33. Ravert, H. T.; Mathews, W. B.; Musachoio, J. L.; Dannals, R. F. J. Labelled Compd. Radiopharm. 1995, 36, 365-371.
34. Lasne, M.-C.; Barré, L.; Huard, C.; Ducandas, C.; McKenzie, E. T. J. Labelled Compd. Radiopharm. 1993, 38, 425-426.
35. Gymer, G. E.; Narayanaswani, S. N. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon Press: Oxford, 1995; Vol. 6, p 443.
36. Marrière, E.; Rouden, J.; Tadino, V.; Lasne, M.-C. Org. Lett. 2000, 2, 1121-1124.
37. Aubert, C.; Huard-Perrio, C.; Lasne, M.-C. J. Chem. Soc., Perkin Trans. 1 1997, 2837-2842 and references therein.
38. (a) Cotarca, L.; Delogu, P.; Nardelli, A.; Sunjic, V. Synthesis 1996, 553-576.
39. (b) Bigi, F., Maggi, R., Sartori, G. Green Chem. 2000, 2, 140-148.
40. (a) Itaya, T.; Kanai, T. Heterocycles 1997, 46, 101-104.
41. (b) Strepikheev, Y. A.; Perlova, T. G.; Zhivechkova, L. A. J. Org. Chem. USSR 1968, 41, 1826-1829.
42. Eckert, H.; Forster, B. Angew. Chem., Int. Ed. Engl. 1987, 26, 894-895.
43. Freer, R.; McKillop, A. Synth. Commun. 1996, 2; 331-349
44. (a) Von Braun, J. Chem. Ber. 1900, 33, 1438-1452.
45. (b) Hageman, H. A. Org. React. 1953, 7, 198-262.
46. For a review on amine dealkylations with acyl chlorides, see: Cooley, J. H.; Evain, E. J. Synthesis 1989, 1-7.
47. (a) Olofson, R. A.; Schnur, R. C.; Bunes, L.; Pepe, J. P. Tetrahedron Lett. 1977, 1567-1570.
48. (b) Olofson, R. A.; Martz, J. T.; Senet, J.-P.; Piteau, M.; Malfroot, T. J. Org. Chem. 1984, 49, 2081-2082.
49. (a) Holtschmidt. H. Angew. Chem. 1962, 74, 848-855.
50. (b) Böhme, H.; Koch, L.; Köhler, E. Chem. Ber. 1962, 95, 1849-1858.
51. (a) Sauter, F.; Stanetty, P.; Hetzl, E.; Furhmann, F. J. Heterocycl. Chem. 1983, 20, 1477-1480.
52. (b) Wolf-Pflugmann, M.; Lambrecht, G.; Wess, J.; Mutschler, E. Arzneim.-Forsch./Drug Res. 1989, 39, 539-544; Chem. Abstr. 1989, 111, 49920.
53. (b) Wolf-Pflugmann, M.; Lambrecht, G.; Wess, J.; Mutschler, E. Arzneim.-Forsch./Drug Res. 1989, 39, 539-544; Chem. Abstr. 1989, 111, 49920.
54. (c) Banholzer, R.; Heusner, A.; Schulz, W. Liebigs Ann. Chem. 1975, 2227-2231.
55. (d) Von Banholzer, R.; Pook, K.-H. Arzneim.-Forsch./Drug Res. 1935, 35, 217-228; Chem. Abstr. 1985, 103, 196293.
56. (d) Von Banholzer, R.; Pook, K.-H. Arzneim.-Forsch./Drug Res. 1935, 35, 217-228; Chem. Abstr. 1985, 103, 196293.
57. (a) Maryanoff, B. E.; Molinari, A. J.; Wooden, G. P.; Olofson, R. A. Tetrahedron Lett. 1982, 23, 2829-2832.
58. (b) Maryanoff, B. E.; Molinari, A. J.; McComsey, D. F.; Maryanoff, C. A. ; Wooden, G. P.; Olofson, R. A. J. Org. Chem. 1983, 48, 5074-5080.
59. (a) Jorand-Lebrun, C.; Valognes, D.; Halazy, S. Synth. Commun. 1998, 28, 1189-1195.
60. (b) During the preparation of our manuscript, another group published a similar study: Banwell, M. G.; Coster, M. J.; Harvey, M. J.; Moraes, J. J. Org. Chem, 2003, 68, 613-616.
61. Howarth, N. M.; Malpass, J. R.; Smith, C. R. Tetrahedron 1998, 54, 10899-10914.
62. See the Supporting Information for complete experimental procedures and characterization data for all new compounds.
63. Baradarani, M. M.; Prager, R. H. Tetrahedron Lett., 1999, 40, 7403-7406.
64. Miller, M. W.; Vice, S. F.; McCombie, S. W. Tetrahedron Lett. 1998, 39, 3429-3432.
65. Majer, P.; Randad, R. S. J. Org. Chem. 1994, 59, 1937-1938.
66. Huang, K.-T.; Sun, C.-M. Biorg. Med. Chem. Lett. 2001, 11, 271-273.
67. See, i.e.: (a) Katritzky, A. R., Pleynet, D. P. M.; Yang, B. J. Org. Chem. 1997, 62, 4155-4158.
68. (b) Lamothe, M.; Perez, M.; Colovray-Gotteland, V.; Halazy, S. Synlett. 1996, 507-508.
69. (a) Ochiai, M.; Kajishima, D.; Sueda, T. Tetrahedron Lett. 1999, 40, 5541-5544.
70. (b) Minisci, F.; Punta, C.; Recupero, F.; Fontana, F.; Pedulh, G. F. J. Org. Chem. 2002, 67, 2671-2676.